I don't know much about the connections between Studs Terkel and Chicago schools, but I know that a lot of people I know knew and admired Studs.
Here's a good place to tell your stories or help others understand his place.
Or, if you feel like listening, here's an NPR segment: Studs Terkel, Oral Historian And Radio Legend, 96 : NPR.
Or, use him in a classroom lesson: Conversations with America.
Or -- last one, I promise -- check out Oklahoma City high school teacher John Thompson's thoughts about him: Education from the Bottom Up.
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